著者

田辺 陽 御前 智則 飯田 聖 西井 良典

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.62, no.12, pp.1249-1259, 2004-12-01 (Released:2009-11-13)

参考文献数

46

被引用文献数

5 7

---

Esterification, sulfonylation, amide formation, and silylations are well recognized as frequently used reactions for organic syntheses. Recent syntheses of fine chemicals and complex natural products, however, require further rationalization of these reactions. We describe herein our recent studies in this area including related representative known methods.(i) Recent progresses of catalytic esterifications are surveyed and we introduce two efficient ammonium triflate catalysts (DPAT and PFPAT) for esterification between 1 : 1 mixture of carboxylic acids and alcohols. (ii) Conventional condensation reagents for esterifications, thioesterifications, and amide formation, are listed and we introduce efficient methods using Me2NSO2Cl/ Me2NR and p-TsCl/N-methylimidazole. (iii) As a promising method for the replacement of conventional pyridine-method, we introduce efficient pyridine-free improved methods, which utilize sterically uncrowded tertiary amines such as Me3N·HCl/Et3N and Me2N (CH2) nNMe2 as a key protocol. (iv) We introduce highly powerful, neutral, and catalytic methods for silylations of alcohols (giving enol ethers) and ketones (giving enol silyl ethers) using hydrosilanes, disilanes, and silazanes.

著者

太田 明広

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.26, no.2, pp.115-131, 1968-02-01 (Released:2009-11-13)

参考文献数

122

被引用文献数

1

著者

松本 澄

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.30, no.12, pp.1035-1042, 1972-12-01 (Released:2009-11-13)

参考文献数

51

被引用文献数

3 3

著者

佐々木 茂貴

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.55, no.7, pp.590-599, 1997-07-01 (Released:2009-11-16)

参考文献数

39

被引用文献数

2 2

---

The triplex formation between the duplex and a single strand DNA has been shown to inhibit transcription at the specific DNA site, and expected as a new biological tool and a new therapeutic method in the so-called antigene strategy. However, native oligonucleotides can form triplexes only within the major groove of the homopurine-homopyrimidine stretch of DNA, and the triplex is destabilized either at a TA or a CG interrupting site. Despite a number of methods have been attempted to expand the limitation of triplex formation, this problem has not been generally solved. This review describes (1) molecular design to stabilize triplex at a TA or a CG interrupting site, including new recognition molecules which have been recently shown by the reviewer and coworkers to be specific toward each base pair. And (2) some method to enhance stability of triplexes with use of DNA binding molecules such as intercalators, cross-linking agents, and groove binders are also discussed.

著者

長谷川 賢

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.25, no.2, pp.116-126, 1967-02-01 (Released:2011-03-01)

参考文献数

74

著者

鈴木 章

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.28, no.3, pp.288-308, 1970-03-01 (Released:2009-11-16)

参考文献数

219

被引用文献数

3 4

著者

杉浦 幸雄

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.39, no.11, pp.1097-1104, 1981-11-01 (Released:2009-11-13)

参考文献数

35

被引用文献数

1

---

Cleavage of cellular DNA by bleomycin substantially contributes to the antitumor activity of this drug. Two characteristics are necessary for antineoplastic action of bleomycin. First, the bithiazole region of the antibiotic has an affinity for the guanine base of DNA. Second, the β-aminoalanine-pyrimidine-β-hydroxyhistidine portion of the drug is capable of oxygen activation by the complexation with Fe (II) ion. The role of the gulose-mannose group and unique interaction between the iron-coordination site and the DNA-binding site have been also indicated. Several spectroscopic data have clearly demonstrated that the bleomycin-Fe (II) complex forms a complex with either CO, C2H5NC, or NO. The “site specific oxygen radical”, produced from an active bleomycin-Fe (II) complex, would account for the action mechanism of selective DNA base cleavage by bleomycin. In addition, the inactivation mechanism of bleomycin hydrolase and important effect of the fifth axial amino group to iron-coordination on bleomycin activity have been discussed.

著者

黒須 三千夫 岸 義人

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.62, no.12, pp.1205-1217, 2004-12-01 (Released:2009-11-13)

参考文献数

37

被引用文献数

6 7

---

The batrachotoxins are a unique class of steroidal alkaloids isolated in minute quantities from the skins of poison arrow frogs (genus Phyllobates) as well as from the skins and feathers of New Guinea birds (genus Pitohui and Iflita) and exhibit various unique structural features, including a steroid-based pentacyclic core skeleton, an intramolecular 3-hemiketal, and a seven-membered oxazapane ring. These compounds are extremely potent neurotoxins (batrachotoxin (2), LD50 in mice 2 μg/kg) that act as selective and irreversible Na+-channel activators. In this paper, we review historical background of isolations and structure determinations of batrachotoxins and our studies on the total synthesis of (-) -batrachotoxinin A (1). Strategic bond-forming events include the stereospecific epoxidation of the double bond (9→10), a new Garst-Spencer protocol to construct 3, 4-disubstituted furan (14b→17b), the stereoselective intramolecular furan Diels-Alder reaction to assemble the steroidal skeleton (20d→22d), a novel intramolecular oxy-Michael reaction to close the oxazapane ring (31→33), an organocerium addition to form the α-enone (39b→40), and the simultaneous reduction and optical resolution of the racemic ketone to provide both enantiomers of a molecule (rac-41→43, 44).

著者

小倉 克之

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.37, no.11, pp.903-913, 1979-11-01 (Released:2009-11-13)

参考文献数

36

被引用文献数

7 6

---

During our investigation to search useful derivatives of dimethyl sulfoxide, we encountered a new sulfoxide, methyl methylthiomethyl sulfoxide which was also named formaldehyde dimethyl dithioacetal S-oxide. Now, this compound is designated conveniently as “FAMSO” by abbreviating he latter name.FAMSO was first synthesized by substitution of chloromethyl methl sulfoxide with a methanethiolate anion and it was later found that this compound could be more easily produced by oxidation of formaldehyde dimethyl dithioacetal with hydrogen peroxide. To date, many papers on organic syntheses using FAMSO have been published and it has appeared to be a versatile reagent for making a variety of organic compounds such as aldehydes, cyclic or acyclic ketones, α-hydroxy aldehydes, α-amino acids, α-keto acids, and α-arylalkanoic acids.This review will disclose the details of the production of FAMSO and its utilization for organic syntheses.

著者

水口 憲哉

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.57, no.1, pp.47-52, 1999-01-01 (Released:2009-11-16)

著者

首藤 紘一 岡本 敏彦

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.32, no.9, pp.670-686, 1974-09-01 (Released:2009-11-13)

参考文献数

95

被引用文献数

4 5

---

環境毒のうちでも発がん性物質ほど恐ろしいものはない.発がん性物質には天然起源のものに加えて, この半世紀の問の有機合成化学の進歩と共に産まれたものも少なくないし, 環境汚染の問題が日を追って重大になっていく昨今, 発がん性物質への理解を高めることは, 合成化学者にとっても, いろいろな意味で必要と思われる.また, ここ数年間の発がん物質の化学・生化学の進歩により, 有機化学的な理解が可能になり, 同時に, ますます有機化学の寄与が求められているのが現状である.本稿では, 化学物質による発がんについての近年の考え方と, 発がん物質の分類と反応性について, 化学的立場からまとめてみたい.

著者

南部 博彦

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.38, no.7, pp.713-718, 1980-07-01 (Released:2009-11-13)

参考文献数

23

---

Thirty years have elapsed since the initial phenol manufacturing process by the auto-oxidation technology was commercialized in Canada, and today, the annual world-wide production of phenol from cumene has reached approximately 3 million tons.Subsequently, the technology of the hydroperoxide process was successfully applied to industrial production of such phenols as cresol and hydroquinone in the 1970's. Furthermore, the commercial manufacture of resorcin using the said technology will be realized in Japan in 1980.Various developments covering the manufacturing process for phenols mentioned above were discussed mainly focussing on the chemical reactions of the respective processes.

著者

田坂 興亜

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.53, no.10, pp.920-921, 1995 (Released:2009-11-16)

著者

Ilies Laurean

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.80, no.11, pp.985, 2022-11-01 (Released:2022-11-05)

著者

西本 能弘 安田 誠

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.80, no.11, pp.1000-1010, 2022-11-01 (Released:2022-11-05)

参考文献数

117

---

In recent years, carbon-fluorine (C-F) bond transformation for organic synthesis has been remarkably developed. Herein, we describe four types of C-F bond transformation mediated by Lewis acids: (1) C(sp2)-F bond transformation of gem-difluoroalkenes through oxyindation/β-fluorine elimination to afford fluorinated isocoumarins; (2) B(C6F5)3-catalyzed substitution of fluorine in 1-fluorostyrenes with silyl ketene acetals via abstraction of F− by in situ generated silylium ions; (3) BF3-catalyzed formal insertion of diazoesters into the C-F bonds of benzylic fluorides; and, (4) photoredox catalyst/Lewis acidic Sn species-mediated C(sp3)-F bond allylation of perfluoroalkylarenes. Density functional theory (DFT) study of the reaction mechanisms suggests the importance of choosing the appropriate Lewis acid to achieve an appropriate activation method for the C-F bonds in each reaction.

著者

小方 芳郎 田伏 岩夫

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.18, no.6, pp.368-387, 1960-06-01 (Released:2010-10-20)

参考文献数

217

被引用文献数

2 1

著者

神谷 佳男

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.26, no.11, pp.957-974, 1968-11-01 (Released:2009-11-13)

参考文献数

152

被引用文献数

2 2

著者

渡辺 一郎

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.46, no.2, pp.169-176, 1988-02-01 (Released:2009-11-13)

参考文献数

20

被引用文献数

2 2

---

Acrylamide is industrially produced by catalytic hydration of acrylonitrile with reduced copper salts. However, the preparation and regeneration of the catalyst are laborious and the process requires a high temperature. It has therefore been considered very desirable to establish a process for producing acrylamide under moderate conditions, because compounds containing double bonds in the molecule are readily polymerizable.There is a growing interest in the synthesis of useful organic compounds by biological process for its specificity and moderate reaction condition. Therefore, we attempted to produce acrylamide from acrylonitrile using microbial enzyme and we found a bacterium having a high acrylamide producing enzyme (nitrile hydratase).This paper describes the details and merits of the development of microbial production of acrylamide.

著者

今田 幸男

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.41, no.11, pp.1008-1017, 1983-11-01 (Released:2009-11-13)

参考文献数

57

被引用文献数

3 4

---

New steroid fermentation processes that produce a variety of intermediates from sterols such as cholesterol and phytosterols have recently been developed.Especially, two fermentation processes for producing intermediates ADD and 4 AD, respectively, have been put into practice for the production of sex hormones and a diuretic drug, spironolactone. New techniques that consist of fermentation processes and the succeeding chemical syntheses are replacing the conventional processes using diosgenin as the starting material.The microbial processes have been accomplished by the isolation of mutants whose metabolic pathway in cholesterol degradation have been blocked by the enzyme deletions that have resulted in the accumulation of a large amount of required intermediates, on the basis of the establishment of the preceding ADD fermentation techniques using chelating agents as inhibitors. Furthermore, for the production of corticoids which are a majority of steroid hormones, some microorganisms supplying useful steroid intermediates have been isolated and some new production routes are now being available.

著者

宇多川 隆 廣瀬 義夫

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.41, no.11, pp.1076-1087, 1983-11-01 (Released:2010-01-22)

参考文献数

48

被引用文献数

3 4

---

Synthesis of biologically interesting nucleosides by a combination of chemical and enzymatic reactions is reviewed. As a likely source of enzyme, Enterobacter aerogenes was selected and its nucleoside phosphorylases were found to catalyze a transglycosyl reaction between pentofuranose and purine or pyrimidine base at relatively high temperature of 60°C. Using this procedure, a variety of nucleoside analogs and nucleosidic antibiotics which have been shown to have antiviral or antitumor activity were synthesized. Noteworthy among them are adenine arabinoside, guanine arabinoside, 2'-amino-2'-deoxyadenosine, 2'-amino -2'-deoxyguanosine and Virazole. It is of special interest that adenine arabinoside can be produced in a good yield with ease and on a large scale. Furthermore, it is reported that the methodology also serves for the preparation of new biologically interesting nucleosides.